864922-12-3Relevant academic research and scientific papers
Enantioselective Synthesis of β-Hydrazino Alcohols Using Alcohols and N-Boc-Hydrazine as Substrates
Cui, Zhihao,Du, Da-Ming
supporting information, p. 5616 - 5619 (2016/11/17)
An enantioselective approach for the synthesis of α-hydrazino aldehydes is described that utilizes alcohols and N-Boc hydrazine instead of the conventional combination of aldehydes with azodicarboxylates. This protocol is enabled by merging in situ aerobic dual oxidation with asymmetric organocatalysis. This reaction also exhibits a high tolerance for varieties of substituents on the alcohol component. This approach features excellent enantiocontrol, cheap starting materials, operational simplicity, and scalability. The corresponding chiral β-hydrazino alcohols were obtained by sequential reduction with excellent enantioselectivity (up to 98% ee).
Metal-templated enantioselective enamine/H-bonding dual activation catalysis
Huo, Haohua,Fu, Chen,Wang, Chuanyong,Harms, Klaus,Meggers, Eric
supporting information, p. 10409 - 10411 (2014/09/17)
An octahedral bis-cyclometalated iridium(III) complex catalyzes the enantioselective α-amination of aldehydes with catalyst loadings down to 0.1 mol%. In this metal-templated design, the metal serves as a structural center and provides the exclusive source of chirality, whereas the catalysis is mediated through the organic ligand sphere. This journal is the Partner Organisations 2014.
Norstatines from Aldehydes by sequential organocatalytic α-amination and passerini reaction
Umbreen, Sumaira,Brockhaus, Manfred,Ehrenberg, Helmut,Schmidt, Boris
, p. 4585 - 4595 (2007/10/03)
The combination of the enantioselective, organocatalytic α-amination of aldehydes by diazodicarboxylates and the Passerini reaction provides rapid access to norstatine-based peptidomimetics. These intermediates were elaborated further by deprotection and cleavage of the N-N bond to provide useful building blocks for aspartic protease inhibitors. Coupling of the compounds 76-86 with the mono-isophthalamide 91 provided moderate inhibitors of human β-secretase (BACE) 92-102. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Enantioselective organocatalytic allylic amination
Poulsen, Thomas B.,Alemparte, Carlos,Jorgensen, Karl Anker
, p. 11614 - 11615 (2007/10/03)
A new strategy for catalytic enantioselective allylic amination based on organocatalysis has been developed. Using a commercially available organocatalyst we demonstrate a direct highly enantioselective allylic electrophilic functionalization of alkyliden
